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I've owned both a 986 Boxster and a 996. Yes, the 996 is more car for the money. However, reading your post it sounds like what you really want is a Boxster. Let that drive your decision more than cost or value.
That said, I will also add that a 987 is miles ahead of a 986. I would suggest you expand your search a bit and look forward in the Boxster line. They kept making the tip through '09 and you can likely get one for around the same price as a nice 996 cab.
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1974 914 Bumble Bee
2009 Outback XT
2008 Cayman S shop test Mule
1996 WRX V-limited 450/1000
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